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Hydroformylation of 1,5‐Hexadiene Catalyzed by Rhodium Complexes in Supercritical Carbon Dioxide and in Toluene: Effects of Fluorinated Phosphane Ligands and Reaction Conditions
Author(s) -
Fujita Shinichiro,
Fujisawa Shinya,
Bhanage Bhalchandra M.,
Ikushima Yutaka,
Arai Masahiko
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300746
Subject(s) - hydroformylation , chemistry , rhodium , toluene , supercritical carbon dioxide , catalysis , supercritical fluid , ligand (biochemistry) , organic chemistry , syngas , trifluoromethyl , yield (engineering) , medicinal chemistry , polymer chemistry , alkyl , biochemistry , receptor , materials science , metallurgy
Rhodium‐catalyzed hydroformylation of 1,5‐hexadiene to dialdehydes was investigated in compressed CO 2 and in toluene using different fluorinated phosphane compounds as ligands at a temperature of 60 °C. Product yields depend greatly on the ligand used and, of the ligands examined, tris[3,5‐bis(trifluoromethyl)phenyl]phosphane is the most effective for the production of dialdehydes both in supercritical CO 2 (scCO 2 ) and in toluene. The total yield of the dialdehydes passes through a minimum at about 9 MPa as the CO 2 pressure is increased and increases appreciably as the H 2 pressure in scCO 2 increases. The effect of the syngas (H 2 /CO) and H 2 pressures on the reaction in scCO 2 is different from that in toluene. It has been suggested that scCO 2 promotes the hydroformylation reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)